Continuing my week through Italy for ATP Finals, I started in Venice and worked west. At the ATP NextGen in Milan, it showcased the top young stars (aged 21 and younger). Happily, it concluded with our hometown hero and San Diego Open champion's victory - Brandon Nakashima.
Waiting to go to Turin (or Torino), I had a couple of days before needing to arrive for the ATP Finals.
![]() |
Paragliding and the Matterhorn. Soaring through Zermatt for the first time. |
Startup's Journey
"No matter what you do, building a start-up will be a very challenging journey…if you don’t start with enough passion, you won’t get to the other side. If you don’t fall in love with the problem, you simply will not be able to get through the journey.”
- Uri Levine (Co-Founder of Waze) "Fall in Love with the Problem" (releases 1/17)
Trying to decide where to go next, I scanned the map and then the weather forecast. November is known for rain and cold weather in that region's shoulder season. Not yet cold enough for snow, yet too cool for most fairweather tourists. Near the Italian/Swiss border was a lifetime bucket list. Marked with a heart on my Google Maps was a mountain called the Matterhorn.
Clear weather to see the mountains
The key luck factor was the weather forecast. It was nothing short of a miracle in November to get clear skies and 50s a high temperature! With just a 48-hour window, it was time to go. Let's do this!
Eagle's Nest
I booked a small AirBnB suite that only crazy backpackers or last-minute cowboys like me even consider. With this once-in-a-lifetime chance, the detour is the adventure. The Obstacle is the Way.
Instead of going South back to Milan, I would detour North to Switzerland. A taxi took me from my Italian castle to the Stresa main train station. This would be the first leg of many to reach Zermatt (basecamp for the Matterhorn). Several trains, buses, shuttles, and lifts later - I would reach the snow.
Lost in Translation
Nobody was working at 6:30 AM, so I only had the option of using the automated Italian train ticket system. I entered my destination, "ZERMATT," and the error screen flashed back several times. "No route found." Uh oh.
I pulled up Google Maps again and saw I'd have to make a few transfers. Reaching Zermatt would take a few different modes of transportation (Italian Train, Swiss Train, Bus, then shuttle).
I ate a quick cafe breakfast and waited outside for the train, faced with 2 platforms - A and B.

Again, there's still no staff at the station. Nobody is working at the window counter. So I ask one lady waiting that looks like she's a local. Was this the platform for the train to Brig?
Brig? No, I think you need to take the other platform.Unfortunately, the "other platform" was for regional trains. The 30 Euro ride I was supposed to take was an express one to connect directly, but because of rail delays, it was actually 15 mins behind.
Accepting my fate, I enjoyed all the little towns along the way. Minutes later, I finally saw my express train whisk by. An elderly gentleman on board kindly explained that I would have to rebook when I arrived at the town of Domodossola. After showing him the translation, he verified my best hope was at the main station.
Switzerland's Ski Resort towns
After my transfer from Brig to Riga, I noticed a big contrast between the surroundings and passengers. This was ski country and early season, so many were going there for a weekend getaway. The Swiss trains were noticeably cleaner, quieter, and better staffed.
On the train, I received an Airbnb text from my host after I told him I'd be behind an hour due to the transfer. He texted back, "no problem - hey, do you want to go paragliding?"
He knew a local guide who could often take his guests up if the weather was clear and the winds were favorable. Apparently, fate wanted me to go fly that day.
Scaling the Matterhorn is a Startup's Journey
![]() |
CES 2023 Eureka Park - Gallery of Flops - the Startup Graveyard |
In the Cold Start Problem, Andrew describes the hundreds of thousands of startups in the US annually, How many actually can get the funding they need to launch? Even pooling the "easy fruit" among the 3 F's: Friends, Family, and Fools, relatively few make it out of the base camp.
Always ready to tell you no or what you can't do.
What you need to find are the lightest feathers for Wings.
Build a solid team that acts as its critical bonding glue.
"The door is going to open for a slipt second. Whether you choose to jump through it or not, it's not going to be there very long."
- James Cameron (MasterClass)
Eternal Optimism - the humbling task of fundraising
Travel teaches you how to rebound from setbacks.
Bruno and the Air Taxi
"I'm Bruno. Follow me - we don't have any time to waste if we are going to catch the next train up!" When I arrived at the meeting point, he informed me this would be a rush.
So immediately before he discussed the price or details, he had me wheel my luggage to his ski office about a half mile away. Luckily, he had an extra pair of snow boots and a parka he could lend me before we ascended.
To fly or to die; there is no try...
You must have some faith you can get the funding you need once you've reached that bridge.
Para-waiting: the patience art of fishing
It is a game of chicken with the wind and nature. Sometimes you prep everything perfectly and get all the details right, yet you don't get your shot. Sometimes it is the right idea, at the wrong time. All you can do is put it all out there and pray to the Wind Gods for the fateful breeze.
Be ready to cast into the falling tide
In the heart of the pandemic or just before reaching the teeth of the Winter, many people get cold feet. TopCourt was a perfect example of a pandemic startup - scaling up when the world was shutting down.
Embrace running against the wind
After 20 or 30 yards, I saw the edge round off and drop down.

It's like waiting for the postman to deliver your college acceptance letter. Waiting weeks or months. Sometimes you expect a possible counter. It feels like an eternity.
Maybe this is how Icarus felt?
Art of letting go, timing the jump, overcoming fear
Commit to your landing zone
Commit to everything you have.
But never celebrate too early before returning to Earth!

Advice for new founders or board advisors
- Join the Stanford LEAD program!
- Take the Business Models Class by Prof Haim.
- The journey starts each Spring and Fall.
Learning to smile again
At some point, you have to accept the facts:
Gravity has you by the balls.
Bank accounts weigh nothing.
As the saying goes...
"Life is short, and so are my legs."
(A few NIH studies about the benefits of being short)
ABC: Awaken, Begin again, and Continue the next climb.
Waiting for the first light to set out is a mistake.
- Reunion with my friend Cristina from Roma
- Meeting the largest racket collector in Europe
- Surviving a bad back on the floor at an Airbnb
- Dealing with Nitto and their 700 Euro corporate seats
- A meeting with tennis travel vlogger, Tsitsipas
- My overall impressions of the ATP Finals for 2023